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A8798 Sigma

Arachidonic acid sodium salt

from porcine liver, ≥99% (capillary GC), waxy solid

Synonym: 5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Sodium arachidonate, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid sodium salt, 20:4

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Properties

Related Categories AN-AZ, Arachidonic Acid, Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
biological source   from porcine liver
InChI Key   DDMGAAYEUNWXSI-XVSDJDOKSA-M
assay   ≥99% (capillary GC)
form   waxy solid
color   white to off-white
solubility   methanol: soluble50 mg/mL, clear, colorless to faintly yellow
shipped in   dry ice
storage temp.   −20°C

Description

Caution

The sodium salts of arachidonic acid are very sensitive to oxidation and will turn yellow and deteriorate rapidly in air. They are packaged under vacuum in sealed ampules. Once opened the product must be used quickly or transferred into an inert atmosphere (dry argon) as soon as possible.

Application

Arachidonic acid is used in assays to measure activity of oxidizing enzymes, such as cyclooxygenase, as well as in assays to determine platelet inhibition in whole blood. AA has been demonstrated to bind to the α subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs), to have a role in the development and progression of prostate cancer, and to enhance formation of lipid bodies in human mast cells.

Biochem/physiol Actions

Released arachidonic acid (AA) reacts with molecular oxygen nonenzymatically, through oxidative stress, and enzymatically through the action of oxygenase enzymes. AA is oxidized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.

General description

Arachidonic acid (AA) is a polyunsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Structurally, it is a 20-carbon chain that contains four cis double bonds, which allow the free acid form of AA to be an insoluble oil; this can be converted to the water-soluble sodium salt form within the normal physiological pH range. AA is metabolized by multiple enzymes to yield various metabolites; AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation and apoptosis.

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Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
JX3874000
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C
Protocols & Articles

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Within mammalian cells, a multitude of lipid compounds are found with a variety of cellular functions, including structural components of cell membranes and as second messengers in cell signaling pat...
Keywords: Absorption, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell signaling, Diabetes, Digestions, Diseases, Growth factors, Hormones, Inflammation, Lipid Metabolism, Lipid signaling, Metabolism

Peer-Reviewed Papers
15

References

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94791 SnapIT Ampule Opener, Regular, for 1-2ml, 5-10ml, 10-15ml ampoules
43917 SnapIT Ampule Opener, large, for 5-10ml, 10-15ml, 20-25ml ampoules

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